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Nuances in fundamental Suzuki−Miyaura cross-couplings employing [Pd(PPh3)4]: poor reactivity of aryl Iodides at lower temperatures
Citation
Ho, CC and Olding, A and Smith, JA and Bissember, AC, Nuances in fundamental Suzuki−Miyaura cross-couplings employing [Pd(PPh3)4]: poor reactivity of aryl Iodides at lower temperatures, Organometallics, 37, (11) pp. 1745-1750. ISSN 0276-7333 (2018) [Refereed Article]
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Copyright Statement
© 2018 American Chemical Society
DOI: doi:10.1021/acs.organomet.8b00189
Abstract
We have explored fundamental Pd-catalyzed Csp2− Csp2 Suzuki−Miyaura cross-couplings of aryl iodides (Ar−I)
employing "classical" Pd/PPh3 catalyst systems. Surprisingly, we observed particularly inefficient couplings of these ostensibly reactive electrophiles in a range of conventional solvent mixtures at lower temperatures (∼50 °C), which was in stark contrast to analogous reactions featuring the equivalent aryl bromides. This feature of well-established Pd/PPh3-mediated Suzuki−Miyaura reactions has received scant attention in the literature. Most significantly, our studies suggest that the inefficient coupling of aryl iodides at lower temperatures derives from the unexpectedly poor turnover of the key on-cycle intermediate trans-[Pd(PPh3) 2(Ar)(I)] (or related PdII−I species) in the presence of PPh3.
Item Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | Suzuki–Miyaura, palladium cross-coupling, aryl iodides, transmetalation processes, ligands |
| Research Division: | Chemical Sciences |
| Research Group: | Inorganic chemistry |
| Research Field: | Transition metal chemistry |
| Objective Division: | Expanding Knowledge |
| Objective Group: | Expanding knowledge |
| Objective Field: | Expanding knowledge in the chemical sciences |
| UTAS Author: | Ho, CC (Dr Curtis Ho) |
| UTAS Author: | Olding, A (Mr Angus Olding) |
| UTAS Author: | Smith, JA (Associate Professor Jason Smith) |
| UTAS Author: | Bissember, AC (Associate Professor Alex Bissember) |
| ID Code: | 126418 |
| Year Published: | 2018 |
| Web of Science® Times Cited: | 7 |
| Deposited By: | Chemistry |
| Deposited On: | 2018-06-12 |
| Last Modified: | 2019-03-06 |
| Downloads: | 57 View Download Statistics |
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